Jessica's Past
by Adoring Pastel Bumblebee
Summary: The start of the series exceptSam pays attention to his dream and tells Jessica about his past bringing her with him and Dean. What happens when Jessica tells Sam about her Supernatural past and Dean wants to steal Jessica from Sam? Humor starts chapter 2
1. Introductions

Sam Winchester woke up screaming for the fourth night in a row.

"What's wrong?" asked a tired Jessica, "Tell me about your dream."

"It's nothing, it just . . ." Sam said unconvincingly, "Nothing."

"Obviously it isn't 'just nothing' if it's been keeping you up for the past four nights," Jessica said bothered that her boyfriend wasn't letting her in. Sometimes she felt like there was a whole other side of him that he didn't want her to see.

Sam fought with himself inside his head on whether he should tell Jessica about his past or not. He wanted her to know, but he didn't want to put her in danger. Finally he gave in and told her deciding that if the dreams he was having were to come true it would be better for her to know.

"So wait . . . you have a brother?" Jessica asked confusedly.

"Yes, his name is Dean and he helps my dad to try and hunt down this . . . this thing that killed my mother," Sam answered.

"So what does this have to do with the nightmares you've been having?" She asked.

"Not nightmares, nightmare," He responded.

"So what's this nightmare?" Jessica asked.

"Well I come home one night, and I'm really exhausted from a trip I'd just taken, so I instantly lay down on the bed. I'm lying there and all of a sudden I feel something dripping on my forehead. I reach up and touch it with my fingers, when I look to see what it is its blood. I look up to the ceiling above my head and you're lying there, just like my mother . . ." Sam trailed off.

"And then what?" Jessica asked.

"Then you burst into flames and I start screaming. That's where I wake up," Sam answered sadly.

"Well don't worry, that isn't going to happen," Jessica said reassuringly. "You aren't going on any trips any time soon, so you can't come back from one to find me dead."

"You know, you're taking this surprisingly well," Sam noticed all of a sudden, "Are you sure you don't think I'm crazy or something?"

"I don't think you're crazy Sam," Jessica said in a serious tone. "I used to have a twin sister named Jennifer, when we were thirteen she started seeing things at night. Everyone just assumed she was imagining things and ignored her, but I saw them too. In the middle of the night when we were alone in our room a . . . I don't even know how to describe this thing . . ." She trailed off.

"Please try, I might be able to tell you what it is," Sam answered.

"How would you know?" Jessica asked interestedly.

"I used to go hunting with my dad and Dean, we've encountered a lot of horrible things," Sam replied.

"Oh . . . okay then I guess," Jessica replied calmly as she began to think back about this thing. "Well . . . it was tall, about nine feet; its head almost touched the ceiling. And it had these glowing purple eyes with no pupils, that was one of the scariest parts. And it had rows and rows of teeth, when it opened its mouth you could see that there were at least ten of them. Its body was dark blue and it was slimy with a tail, it had two webbed feet, but also two without webbing." Jessica paused shuddering at the thought of the creature.

"It would show up in our room every night, one second it wasn't there, the next it was standing by Jenny's bed. The first few times it just stood there and disappeared the same way it came at one in the morning. But then it started to whisper her name over and over for the whole hour it was there, 'Jenny . . . Jenny . . .' its voice was inhuman, it was like nails on a chalk board. After a while it began to tell her how it was going to kill her by scratching her throat open over and over with plenty of detail, and right before it left it would come over to my bed and whisper 'If you tell anyone I'll kill you too,' then disappear." Jessica said.

"So what happened to your sister?" Sam asked curiously.

"Well when she told our parents they didn't believe her, but after a while they discovered that she was truly terrified and believed what she was saying, so they took her to therapy. I never told anyone what I'd seen because I was too scared, in fact once the therapist brought me in for a session and asked if I saw it and I said no." Jessica was crying now.

"And then one night I was at a friend's sleepover and when I came home the next morning Jenny was dead, her throat scratched open. And the worst part is that everyone believed that she had done it to herself. They said it was just a sad story and that she was mentally unstable and when forced to sleep in a room alone she just snapped and started scratching at her throat. But I know that that's not what happened," Jessica finished.

Sam held her close trying to comfort her while she cried.

After several minutes she stopped crying and looked up at Sam, "Do you know what did it?" she asked hopefully.

"I'm sorry, but I don't," he replied, "But trust me I'll find it."

Half an hour later the couple woke up to the footsteps of someone in the living room.

"Follow me," Sam whispered to Jessica as he got out of bed and walked into the hallway.

When they got to the living room Sam saw a shadowy figure standing in front of him and instantly attacked. They fought for a couple minutes while Jessica stood in shock until she found the light switch and turned the light on.

"Dean?" Sam asked surprised.

"Yeah, now get off of me," Dean responded irritated.

After both of the men stood up Sam introduced Jessica and Dean to each other. Holy crap she's perfect, thought Dean, it just figures that Sam's already taken her.

"Just call me Jess," Jessica said kindly to her boyfriend' brother, "I'm just going to go throw some clothes on."

"Oh, no please don't," flirted Dean, "I like the Smurfs."

Dean turned to Sam and said, "If only there were two of her!"

Jessica instantly ran over to where Dean stood and bitch-slapped him across the face as hard as she could.

"What the hell was that for?" Dean asked.

"She used to have a twin," Sam answered pulling Jessica away from Dean and holding her hand.

"Oops," Dean responded embarrassedly.

A few moments of awkward silence went by before Sam asked, "So why are you here breaking into my apartment at four in the morning anyways?"

"Oh right," Dean responded, "I need to talk to you alone."

"Whatever you're going to say you can say in front of Jess," Sam said sternly.

"Ok," Dean said, "Dad's on a hunting trip, and he hasn't been home in a few days."

Shock spread across Sam's face.

"Wait you mean like with . . ." Jess, who was very new to this, trailed off.

"Yeah with ghosts and stuff," Sam replied.

"Wait you told her!" Dean said angrily.

"Yeah, and she's coming with us," Sam answered surprising both Dean and Jess.

**A/N: ****Ok this is my first chapter of my first story so go easy on me. If you want me to write more please review, I'd love to hear your input. Thanks for reading! Also a very special thanks to Mrs. Dr. Robert Chase who beta-readered this chapter for me!**


	2. Dean Makes Everything Awkward

"I'm so bored," Jess whined from the back of Dean's car, "Let's play a game!"

"Sure, how about Have You Ever?" Dean replied happily. "Only everyone has to answer each question."

"All right Dean . . . I've got one," replied Sam. "Have you ever disobeyed your dad?"

"Yeah," they all answered.

"Have you ever kissed a girl?" asked Dean.

"Duh," responded Sam.

"Yeah," said Jessica blushing causing Dean to grin.

"So have I," responded Dean.

"Have you ever . . ." Jessica started. "Killed a ghost?"

"Yup," they both responded.

"I haven't," she said.

"Have you ever," Sam began . . . "Been in a committed relationship?"

"Obviously," Jess responded knowing that this comment was directed at Dean.

"Yeah," Dean said defensively.

"You're lying," Sam said critically.

"If that's the way we're going to play," Dean responded angrily. "Then how about this, have you slept with Sam? I haven't."

"You don't have to answer that Jess!" Sam said angrily punching Dean in the arm.

"Pervert!" Jess said annoyed and slapped Dean in the back of the head.

After an hour of awkward silence other than Dean occasionally complaining about everyone hitting him, everybody became very bored.

"How about we play Would You Rather?" Asked Jess. "But nothing stupid Dean."

"Fine," Dean agreed.

"Okay," replied Sam, "Dean, would you rather. . . Kiss a guy or never kiss a girl again?"

"That depends on who it is, for how long, and whether it has to have tongue." Dean responded.

"Ok," Sam said starting to smirk, "Michael Jackson, thirty seconds, full tongue."

"Hell no! I'd choose never kiss a girl!" Dean said. "Jess would you rather get a sex change or date someone who got one?"

"Sam you're really a guy right?" Jess asked.

"Yup," he answered.

"Then I'd get a sex change I guess. It would be too gross trying to figure out what gender to classify them as," Jess said.

Sam shuddered at the thought of Jess as a man.

"Ok Sam, would you rather swim in a pool of human blood for an hour or lick up someone else's vomit?" Jess asked grinning.

"Ugh . . . Pool of blood," Sam said as Dean laughed.

"Jess, would you rather be trapped in an elevator with ten Deans hitting on you for one night or by yourself for three?" Sam asked.

"Ten Deans, at least there'd be some entertainment, plus I could become a cannibal without feeling bad," Jess responded sarcastically.

"Dean would you rather wake up with two d-cups that you couldn't surgically remove or with no testicles which you couldn't surgically replace?" She asked with a grin.

"Oh come on!" Dean said angrily, "I guess . . . no testicles."

Sam and Jess started to laugh as hard as they could.

"Sam, would you rather be in a porn movie or watch gay porn with dad that he's in?" Dean asked.

"What the hell kind of question is that?" Sam asked.

"You have to answer Sammie," Dean replied.

"Fine . . . I guess be in a porno," Sam said annoyed. "Dean, would you sleep with a homeless man or sleep with Carrot Top?"

"Jesus Christ, I think I'd have to choose the hobo," Dean answered disgustedly. "Jess, would you rather have Sam die and never be with another man again or break Sam's heart and marry me?"

"It's alright if you kill me," Sam said.

"Umm . . . I guess break Sam's heart," Jess responded, "But I'd divorce you and take all your money!"

"Well bad news hun, I don't have any money!" Dean said in a bragging tone.

The three continued to play Would You Rather for another half hour before they got bored of it.

After a while Dean suggested that they play truth or dare.

"In the car?" asked Sam.

"Sure why not we'll just make dares that can be done in the car," Dean answered.

"Sam truth or dare?" asked Jess.

"Dare, we've basically been playing truths for the whole trip," Sam answered.

"Okay, you have to take your shirt off and wear one of the bras I brought with me for the next fifteen minutes," Jess said grinning passing him a pink lacy bra.

After Sam was in his bra, it was his turn to ask someone. "Dean truth or dare?"

"Dare," Dean replied.

"I dare you to lick the bottom of my shoe for a minute straight," Sam said removing his stinky left shoe.

"Aw nasty," Dean responded, but agreed to do it after several minutes of persuasion and pulled over to the side of the road.

When the minute was up Dean looked like he was about to throw up and Jess was laughing at the looks on the people in the cars driving by's faces.

Before pulling back on to the road Dean pulled a pack of gum out of his pocket and popped all six pieces into his mouth. By the time they had begun to drive Sam was allowed to take the bra off and quickly changed back into his shirt.

"Jess truth or dare?" Dean asked.

"Dare," she responded happily.

Dean thought it over for a few minutes then pulled into the parking lot of a gas station.

"I dare you to kiss me." He said with a straight face.

**A/N: Thanks to those who have added story alerts to this story! I know it's taken a while to update, but with no reviews I'm not very motivated to continue. So please if you want me to continue send in a review! Also a special thanks to Mrs. Dr. Robert Chase for beta-reading this chapter as well as the first one!**


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